By Baila Sebrow

By Baila Sebrow


I’d like some advice on getting a relationship to get off the ground.

I reside in Boro Park. I am in my mid-forties and have been divorced for many years. I am blessed to have two invitations every week for Shabbos. Since many open their doors to singles, I often see the same circle of individuals on a regular basis. Among this circle, Sima (not her real name) is someone who has caught my eye for her appearance, wit, and humor.

She grew up in a frum community, not in Brooklyn, and today she is in her upper fifties. Her father was the rav of a shul, and out of respect for him, she agreed to marry a fellow with whom she was set up. He treated her horribly and the marriage lasted six months. Sima has a college degree and has worked for a recruiter in a frum organization, as well as in nursing homes.

A couple of years ago, I appealed to a member of the “Shabbos table chevra” to see if a shidduch is possible. Even though Sima declined through the mutual third party, she has since then always started some small talk with me when we meet in person. Just this past Shabbos, we sat next to each other at a tight Shabbos table and Sima brought to my attention that she is a lefty. During the Shabbos meal, she asked me why Shavuos has no chol ha’moed. However, the mystery to me is: Why is it when I try to reach Sima (via e-mail, text, or Facebook) during the week I get no response?

I would be delighted to hear your advice, recommendation, and feedback on how to proceed.


This might be a bitter pill to swallow, and I am sorry to have to tell you, but it does not sound like Sima wants to date you. In the back of your mind, you might have even considered that, but it appears to you that she is sending you mixed signals. I don’t know what Sima is really thinking, as I only have your information to go by.

I must first comment on the community that you are blessed and lucky to live in and be made to feel a part of. There are plenty of singles living in frum communities who sit home week after week, all by themselves, without any invitation. Kudos to those families who open their homes to singles every Shabbos to create a “Shabbos table chevra.” You are extremely fortunate!

As a shadchan I am oftentimes asked to step into situations where someone was declined for a shidduch. At times it might be because the suggestion was initially not performed properly, and so when I step in, I make sure that whatever was done and said by the previous person playing matchmaker has no bearing on the outcome of the shidduch. However, those circumstances are not as common as when the person being asked out does not feel that the shidduch is compatible. There were situations where I was told by a single man or woman that I am one of several people attempting to arrange a match with so-and-so. Some have even expressed that they are beginning to feel harassed. I can see why they feel that way. Nobody wants to be in the position of having to decline a shidduch more than once.

It sounds like you have made more than one attempt. The first one through that third party, and then you mentioned three other attempts: e-mail, text, and Facebook. Moreover, I have a hunch that in each of those examples, you made attempts to communicate with Sima more than once. You might believe that all your efforts to pursue her are appreciated, but instead you are likely making her feel very uncomfortable.

She is nice to you at the meals and she initiates conversations; she likely values the invitations by the hosts you both share and does not want to do anything that could possibly jeopardize her relationship with them, so she is being nice, and maybe even extra-nice to you. I advise you to back off from asking anyone else to reach out to her, and you need to stop trying to contact her. As much as you like her, and you believe there is compatibility, she does not seem to agree.

Please understand that a rejection from a particular person may not even have anything to do with you as a person, or her lack of attraction to you, but rather something different. You stated that you are in your mid-forties, and she is in her upper-fifties. Though you might believe that she should feel flattered by your interest, it is possible that she is looking for a man closer to her in age. Or it could be a hashkafic matter. Maybe she wants somebody more modern or more to the right. We should also consider two other options: It is not a given that every single man or woman is seeking a relationship leading to marriage. There are plenty of singles who prefer to live out their life in their status quo. The other consideration is that unbeknownst to everyone else, there is a chance that she might already have a significant other in her life. I am mentioning all these scenarios (and it is possible there could be other explanations) for your own peace of mind and to give you healthy closure.

Continue being polite to this lady at your Shabbos meals. Do not try to sit next to her. If she wants to sit next to you because she simply enjoys your company at meals, then it needs to be her choice. Maybe one day, she might change her mind—or not. You have been proactive in pursuing her, so feel confident in the knowledge that you have done your utmost in hishtadlus with regard to this shidduch possibility. For now, you need to move forward.

If you had been in a relationship with this lady, I would not have advised you to continue going to those Shabbos meals and be polite. That could only lead to feelings of anxiety before each meal and even depression after the meal. Such situations turn into vicious cycles where the person rejected cannot move on. In this case, you have not even dated her. However, I don’t know if you developed emotional feelings for her. I am hoping that you didn’t, and you are just in the midst of a strong interest in her. You need to take stock of what you are really experiencing. If you can manage to sit next to her and have a platonic conversation, then continue doing so. If you do not have the emotional capacity to do that, try to find another host so that you can put that space between you and her until you heal.

Rejection is hard even on the most resilient person. Your self-esteem takes a hit, and it can sting like physical pain. As I said earlier, oftentimes it is not personal. But that doesn’t mean that you should be living with false hope either. To help you cope, get out there and meet other women. It sounds like you have a wide social circle. Get the word out there that you are no longer hung up on that woman (to those who know about your interest in her) and that you are a marriage-minded man looking to remarry.

Do not allow this rejection or any other to define who you are. Do not allow your self-worth to become dependent on anyone else’s opinion of you. You may already know what you have to offer, or ask a friend or family member to outline all your positive qualities that you can bring into a relationship and marriage. Ask them also what areas could use improvement, and work on those aspects. Begin to believe in yourself to the extent that you will think that you are the next best thing to sliced bread! The way one feels about himself is the image he presents to the world. Know that you are the best, and you will attract the best for you.


Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. She can be reached at Baila also hosts The Definitive Rap podcast for, Israel News Talk Radio, WVIP 93.5 FM HD2, and Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles at


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